Use of 8,8'-dihydroxy-1,1'-binaphthalene as a chiral auxiliary for asymmetric Diels-Alder cycloadditions

Tetrahedron Asymmetry

Volumn 8, Issue 21, 1997, Pages 3637-3645

  Tanaka, Kiyoshi ^a   Asakawa, Naoyuki ^a   Nuruzzaman, Mohammad ^a   Fuji, Kaoru ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8,8' DIHYDROXY 1,1 BINAPTHALENE; CYCLOPENTADIENE DERIVATIVE; FUMARIC ACID; HYDROXYL GROUP; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; ENVIRONMENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 0031566725     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00474-6     Document Type: Article

References (29)

1. 1. a) Noyori, R. in Asymmetric Catalysts in Organic Synthesis, Wiley, New York, 1994.
2. b) Rosini, C.; Franzini, L.; Raffaelli, A.; Salvatori, P. Synthesis 1992, 503.
3. c) Kaufmann, D.; Boese, R. Angew. Chem. Int. Ed. Engl. 1990, 29, 545.
4. 2. a) Artz, S. P.; de Grandpre, M. P.; Cram, D. J. J. Org. Chem. 1985, 50, 1486.
5. b) Peacock, S, S.; Walba, D. M.; Gaeta, F. C. A.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1980, 102, 2043.
6. c) Cram, D. J.; Sogah, G. D. Y. J. Chem. Soc., Chem. Commun. 1981, 625.
7. 3. Fukushi, Y; Shigematsu, K.; Mizutani, J.; Tahara, S. Tetrahedron Lett. 1996, 37, 4737.
8. 4. Fuji, K.; Kawabata, T.; Kuroda, A. J Org. Chem. 1995, 60, 1914.
9. 5. Fuji, K.; Yang, X.-S.; Tanaka, K.; Asakawa, N.; Hao, X.-J. Tetrahedron Lett, 1996, 37, 7373.
10. 6. a) Seyden-Penne, J. in Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995, chap. 9.
11. b) In Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Ed. Pergamon Press, Oxford, 1991, vol. 5, chap. 4.1 to 4.4.
12. c) Carruthers, W. in Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990.
13. 7. Fabbi, D.; Delogu, G.; Lucchi, O. D. J. Org. Chem. 1995, 60, 6599.
14. 8. Inanaga, J.; Hirata, K.; Saeki, H.: Katsuki, T.; Yamaguchi, M. Bull. Soc. Chem. Jpn. 1979, 52 , 1989.
15. 9. Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
16. 10. Sunaga, T.; Iven, K.; Hormeister, G.; Oskam, J.; Schrock, R. Macromolecules 1994, 27, 4043.
17. 11. a) Lewis, F. D.; Oxman, J. D. J. Am. Chem. Soc. 1984, 106, 466.
18. b) Loncharich, R. J.; Schwartz, T. R., Houk, K. N. ibid. 1987, 709, 14.
19. 12. a) Prelog, V. Helv. Chim. Acta 1953, 36, 308.
20. b) Prelog, V.; Tsatsas, G. ibid. 1953, 36, 1178.
21. 13. Pascual-Teresa, B. de; Gonzalez, J.; Asensio, A.; Houk, K. H. J. Am. Chem. Soc. 1995, 117, 4347.
22. 14. a) Shambayati, S.; Schreiber, S. L. in Comprehensive Organic Synthesis, Trost, B. M. and Fleming, I. Ed. Pergamon Press, Oxford, 1991, vol. 1, chap. 1.10.
23. b) Narasaka, K. Synthesis 1991, 1.
24. c) Aitken, R.; Gopal, J. Tetrahedron: Asymmetry, 1990, 1, 517.
25. 15. a) Poll, T.; Hady, A. F. A.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5595.
26. b) Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. ibid. 1985, 26, 3095.
27. c) Poll, T.; Metter, J. O.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1985, 24, 112.
28. 16. a) Torrens, F.; Ruiz-López, M.; Cativiela, C.; Garcia, J. I.; Mayoral, J. A. Tetrahedron 1992, 48, 5209.
29. b) Waldmann, H. J. Org. Chem. 1988, 53, 6133.